US4992571A - Method for making octyloxy substituted diphenyl iodonium hexafluoro metalloid salts - Google Patents
Method for making octyloxy substituted diphenyl iodonium hexafluoro metalloid salts Download PDFInfo
- Publication number
- US4992571A US4992571A US07/429,744 US42974489A US4992571A US 4992571 A US4992571 A US 4992571A US 42974489 A US42974489 A US 42974489A US 4992571 A US4992571 A US 4992571A
- Authority
- US
- United States
- Prior art keywords
- octyloxyphenyl
- phenyliodonium
- tosylate
- salt
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/90—Antimony compounds
- C07F9/902—Compounds without antimony-carbon linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
Definitions
- diaryliodonium salts such as diphenyliodonium hexafluoroantimonate were prepared by effecting reaction between an intermediate diarylhalonium bisulfate and an alkylhexafluoro salt, such as diphenyliodonium hexafluoroantimonate.
- the present invention is based on the discovery that (octyloxyphenyl) phenyliodonium hexafluoroantimonate can be made by a one pot procedure involving the employment of a phase transfer catalyst in the initial synthesis of the n-octylphenyl ether, followed by the removal of the aqueous basic solution from the initial synthesis mixture. Phenyl iodide and a peracid can be added directly to the n-octylphenyl ether followed by the addition of p-toluene sulfonic acid in the same reaction vessel.
- the resulting hydroxy (tosyloxy) iodobenzene which forms, reacts in situ with the n-octylphenyl ether while the temperature is maintained at about 30° C. or below.
- Recovery of the resulting (octyloxyphenyl) phenyliodonium tosylate can be achieved by extracting the reaction mixture with an organic solvent and water and triturating the reaction mixture with aliphatic hydrocarbon solvent.
- the metathesis of the (octyloxyphenyl) phenyliodonium tosylate and an alkali metal hexafluoroantimonate salt can be effected in the same vessel.
- (octyloxyphenyl) phenyliodonium hexafluorometalloid salt means the corresponding hexafluoroantimonate, hexafluorophosphate, or hexafluoroarsenate salt.
- a one pot method for making an (octyloxyphenyl) phenyliodonium hexafluorometalloid salt which comprises,
- n-octylphenyl ether is initially synthesized by effecting reaction between 1 to 3 mols of phenol, per mol of a halooctane such as 1-bromooctane in the presence of a phase transfer catalyst, for example tetrabutylammoniumbromide, cetylammonium chloride, and trimethylbenzylammonium chloride, an inert organic solvent, for example, toluene, benzene, xylene, chlorobenzene, n-hexane, n-heptane, n-octane, dichloromethane, and an aqueous alkali metal hydroxide solution, such as sodium or potassium hydroxide.
- a phase transfer catalyst for example tetrabutylammoniumbromide, cetylammonium chloride, and trimethylbenzylammonium chloride
- an inert organic solvent for example, toluene, benzene,
- the reaction mixture can be agitated and refluxed for a period of from 3 to 36 hours and then allowed to cool to room temperature.
- the aqueous layer can be removed by decantation and the organic layer can be extracted with an alkali metal hydroxide solution with water thereafter the organic solvent can be removed under reduced pressure.
- Iodobenzene can be added to the same pot containing the n-octylphenyl ether in substantially equal molar amounts at temperatures in a range of from 0° C. to 60° C.
- a suitable peracid such as peracetic acid, perbenzoic acid, m-chloroperbenzoic, or perphthalic acid can be added gradually to the resulting mixture of iodobenzene and n-octylphenyl ether while it is being stirred and maintained at a temperature of 20° C. to 40° C. over a period of from 15 to 120 minutes.
- the reaction mixture can be agitated for an additional 1 to 30 hours.
- a toluenesulfonic acid such as p-toluenesulfonic acid can then be added to the mixture which can be agitated for an additional 1 to 8 hours.
- the heterogeneous reaction mixture then can become homogeneous, and the mixture can turn orange after a short period of time.
- Various workup procedures can be used to recover the (octyloxyphenyl) phenyliodonium tosylate from the reaction mixture prior to the addition of the alkali metal hexafluorometalloid salt.
- One procedure involves the addition of an inert organic solvent, such as toluene and water to the reaction mixture while it is agitated, followed by the separation of the aqueous layer and extraction thereof with an inert organic solvent.
- the organic solvent extract can be combined with the original organic phase.
- the organic solvent layer can then be extracted once with water followed by treatment with an aliphatic hydrocarbon solvent, such as n-heptane or n-octane to effect the precipitation of the desired tosylate product which can be an off-white solid.
- Another procedure which can be used to recover the (octyloxyphenyl) phenyliodonium tosylate is triturating the reaction mixture with an aliphatic hydrocarbon, such as heptane followed by decanting the aliphatic hydrocarbon from the resulting orange oil.
- An aliphatic hydrocarbon such as heptane
- a second trituration with the aliphatic hydrocarbon can be used followed by triturating with water at least twice.
- the resulting solvent can then be triturated once more with the aliphatic hydrocarbon and thereafter filtered and washed.
- An additional work-up procedure which can be employed to recover the (octyloxyphenyl) phenyliodonium tosylate product is to initially add with stirring an inert aromatic organic solvent, such as toluene, to the reaction mixture with an equal volume of water followed by separating the aqueous layer and extracting it once with the aromatic organic solvent.
- the tosylate product can then be extracted once with water; thereafter the solvent can be removed under reduced pressure resulting in an orange solid.
- the orange solid can be broken up and triturated with the aliphatic organic solvent, such as heptane, filtered and washed again with the aliphatic organic solvent.
- the metathesis reaction can be effected with a mixture of an inert organic solvent, such as acetone and an alkali metal hexafluorometalloid salt, such as the corresponding hexafluoroantimonate, hexafluorophosphate or hexafluoroarensate, referred to hereinafter as the hexafluoroantimonate salt.
- the hexafluoroantimonate salt can be added to the (octyloxyphenyl) phenyliodonium tosylate followed by agitating the resulting mixture for a period of from 15 to 180 minutes. The mixture can then be filtered and then added to an excess amount of distilled water.
- the resulting oil can then be triturated with water and the water decanted followed by the addition of further amounts of water.
- the mixture can then be stirred for another 15 to 180 minutes and the water decanted and an inert aliphatic solvent such as n-heptane or n-octane can be added.
- an inert aliphatic solvent such as n-heptane or n-octane can be added.
- the reaction mixture was triturated twice with 70 ml of water and once with 70 ml of n-heptane. After each wash the solvent was filtered from the solid product. It was then added to the resulting mixture 60 ml of acetone and 9.4 grams of sodium hexafluoroantimonate while the mixture was stirred for an additional 30 minute period. The acetone solution was then filtered and the acetone mixture was added to 500 ml of distilled water. There was obtained an oil which was triturated for 5 minutes and the water was decanted and 200 ml of fresh water was added. After stirring for another 5 minutes, the water was decanted and 200 ml of heptane was added.
- the (4-octyloxyphenyl) phenyliodonium hexafluoroantimonate salt is found to be useful as a photo initiator for 4-vinylcyclohexene dioxide when employed at about 3% by weight using a GEH3T7 lamp at a distance of 6 inches at an exposure of about 1 second.
Abstract
Description
Claims (6)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/429,744 US4992571A (en) | 1989-10-31 | 1989-10-31 | Method for making octyloxy substituted diphenyl iodonium hexafluoro metalloid salts |
CA002023392A CA2023392A1 (en) | 1989-10-31 | 1990-08-16 | Method for making octyloxy substituted diphenyl iodonium hexafluoro metalloid salts |
AT90120047T ATE110706T1 (en) | 1989-10-31 | 1990-10-19 | PROCESS FOR THE PREPARATION OF OCTYLOXY- SUBSTITUTED DIPHENYLIODONIUM HEXAFLUOROMETALLOID SALTS. |
DE69012047T DE69012047T2 (en) | 1989-10-31 | 1990-10-19 | Process for the preparation of octyloxy-substituted diphenyl iodonium hexafluorometalloid salts. |
EP90120047A EP0425920B1 (en) | 1989-10-31 | 1990-10-19 | Method for making octyloxy substituted diphenyl iodonium hexafluoro metalloid salts |
FI905354A FI905354A0 (en) | 1989-10-31 | 1990-10-30 | FOERFARANDE FOER FRAMSTAELLNING AV OKTYLOXISUBSTITUERADE DIFENYLJODONIUMHEXAFLUORMETALLOIDSALTER. |
JP2292219A JPH0751524B2 (en) | 1989-10-31 | 1990-10-31 | Preparation of octyloxy-substituted diphenyliodonium hexafluorometalloid salts |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/429,744 US4992571A (en) | 1989-10-31 | 1989-10-31 | Method for making octyloxy substituted diphenyl iodonium hexafluoro metalloid salts |
Publications (1)
Publication Number | Publication Date |
---|---|
US4992571A true US4992571A (en) | 1991-02-12 |
Family
ID=23704556
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/429,744 Expired - Lifetime US4992571A (en) | 1989-10-31 | 1989-10-31 | Method for making octyloxy substituted diphenyl iodonium hexafluoro metalloid salts |
Country Status (7)
Country | Link |
---|---|
US (1) | US4992571A (en) |
EP (1) | EP0425920B1 (en) |
JP (1) | JPH0751524B2 (en) |
AT (1) | ATE110706T1 (en) |
CA (1) | CA2023392A1 (en) |
DE (1) | DE69012047T2 (en) |
FI (1) | FI905354A0 (en) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2688783A1 (en) * | 1992-03-23 | 1993-09-24 | Rhone Poulenc Chimie | NOVEL BORONES OF ONIUM OR ORGANOMETALLIC COMPLEX CATIONIC PRIMERS FOR POLYMERIZATION. |
US5286612A (en) * | 1992-10-23 | 1994-02-15 | Polaroid Corporation | Process for generation of free superacid and for imaging, and imaging medium for use therein |
US5334489A (en) * | 1992-10-23 | 1994-08-02 | Polaroid Corporation | Process for generation of squaric acid and for imaging, and imaging medium for use therein |
US5401607A (en) * | 1991-04-17 | 1995-03-28 | Polaroid Corporation | Processes and compositions for photogeneration of acid |
US5441850A (en) * | 1994-04-25 | 1995-08-15 | Polaroid Corporation | Imaging medium and process for producing an image |
US5488147A (en) * | 1994-07-21 | 1996-01-30 | Minnesota Mining And Manufacturing Company | Diaryliodonium fluoroalkyl sulfonate salts and a method of making |
US5582956A (en) * | 1994-04-25 | 1996-12-10 | Polaroid Corporation | Process for fixing an image, and medium for use therein |
US5914213A (en) * | 1996-11-27 | 1999-06-22 | Polaroid Corporation | Process and composition for generation of acid |
US6015907A (en) * | 1996-11-27 | 2000-01-18 | Polaroid Corporation | Trisubstituted pyridine dyes |
US6110638A (en) * | 1996-11-27 | 2000-08-29 | Polaroid Corporation | Process and composition for generation of acid |
US6147184A (en) * | 1992-03-23 | 2000-11-14 | Rhone-Poulenc Chimie | Onium borates/borates of organometallic complexes and cationic initiation of polymerization therewith |
US20080051553A1 (en) * | 2005-09-20 | 2008-02-28 | General Electric Company | Thermally curable compositions and method |
EP2236488A1 (en) | 2001-03-30 | 2010-10-06 | The Arizona Board of Regents on behalf of the University of Arizona | Materials, methods and uses for photochemical generation of acids and/or radical species |
US8343608B2 (en) | 2010-08-31 | 2013-01-01 | General Electric Company | Use of appended dyes in optical data storage media |
CN104628540A (en) * | 2013-11-08 | 2015-05-20 | 上海予利化学科技有限公司 | Cation photoinitiator (4-octyloxyphenyl)phenyl iodonium hexafluoroantimonate preparation method |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4058400A (en) * | 1974-05-02 | 1977-11-15 | General Electric Company | Cationically polymerizable compositions containing group VIa onium salts |
US4310469A (en) * | 1978-12-29 | 1982-01-12 | General Electric Company | Diaryliodonium salts |
US4399071A (en) * | 1982-03-12 | 1983-08-16 | General Electric Company | Method for making diaryliodonium salts |
US4537725A (en) * | 1982-09-18 | 1985-08-27 | Ciba-Geigy Corporation | Diaryliodosyl salts |
US4933377A (en) * | 1988-02-29 | 1990-06-12 | Saeva Franklin D | Novel sulfonium salts and the use thereof as photoinitiators |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3981897A (en) * | 1975-05-02 | 1976-09-21 | General Electric Company | Method for making certain halonium salt photoinitiators |
US4882201A (en) * | 1988-03-21 | 1989-11-21 | General Electric Company | Non-toxic aryl onium salts, UV curable coating compositions and food packaging use |
-
1989
- 1989-10-31 US US07/429,744 patent/US4992571A/en not_active Expired - Lifetime
-
1990
- 1990-08-16 CA CA002023392A patent/CA2023392A1/en not_active Abandoned
- 1990-10-19 EP EP90120047A patent/EP0425920B1/en not_active Expired - Lifetime
- 1990-10-19 AT AT90120047T patent/ATE110706T1/en not_active IP Right Cessation
- 1990-10-19 DE DE69012047T patent/DE69012047T2/en not_active Expired - Fee Related
- 1990-10-30 FI FI905354A patent/FI905354A0/en not_active Application Discontinuation
- 1990-10-31 JP JP2292219A patent/JPH0751524B2/en not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4058400A (en) * | 1974-05-02 | 1977-11-15 | General Electric Company | Cationically polymerizable compositions containing group VIa onium salts |
US4310469A (en) * | 1978-12-29 | 1982-01-12 | General Electric Company | Diaryliodonium salts |
US4399071A (en) * | 1982-03-12 | 1983-08-16 | General Electric Company | Method for making diaryliodonium salts |
US4537725A (en) * | 1982-09-18 | 1985-08-27 | Ciba-Geigy Corporation | Diaryliodosyl salts |
US4933377A (en) * | 1988-02-29 | 1990-06-12 | Saeva Franklin D | Novel sulfonium salts and the use thereof as photoinitiators |
Cited By (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5401607A (en) * | 1991-04-17 | 1995-03-28 | Polaroid Corporation | Processes and compositions for photogeneration of acid |
US5468902A (en) * | 1992-03-23 | 1995-11-21 | Rhone-Poulenc Chimie | Onium borates/borates of organometallic complexes and cationic initiation of polymerization therewith |
EP0562897A1 (en) * | 1992-03-23 | 1993-09-29 | Rhone-Poulenc Chimie | Borates with cations selected from the group of onium or organometallic complexes, as cationic polymerisation initiators |
US6153661A (en) * | 1992-03-23 | 2000-11-28 | Rhone-Poulenc Chimie | Onium borates/borates of organometallic complexes and cationic initiation of polymerization therewith |
US6147184A (en) * | 1992-03-23 | 2000-11-14 | Rhone-Poulenc Chimie | Onium borates/borates of organometallic complexes and cationic initiation of polymerization therewith |
US5668192A (en) * | 1992-03-23 | 1997-09-16 | Rhone-Poulenc Chimie | Onium borates/borates of organometallic complexes and cationic initiation of polymerization therewith |
US5550265A (en) * | 1992-03-23 | 1996-08-27 | Rhone-Poulenc Chimie | Onium borates/borates of organometallic complexes and cationic initiation of polymerization therewith |
FR2688783A1 (en) * | 1992-03-23 | 1993-09-24 | Rhone Poulenc Chimie | NOVEL BORONES OF ONIUM OR ORGANOMETALLIC COMPLEX CATIONIC PRIMERS FOR POLYMERIZATION. |
US5445917A (en) * | 1992-10-23 | 1995-08-29 | Polaroid Corporation | Imaging medium |
US5334489A (en) * | 1992-10-23 | 1994-08-02 | Polaroid Corporation | Process for generation of squaric acid and for imaging, and imaging medium for use therein |
US5578424A (en) * | 1992-10-23 | 1996-11-26 | Polaroid Corporation | Process for generation of unbuffered super-acid and for imaging |
US5395736A (en) * | 1992-10-23 | 1995-03-07 | Polaroid Corporation | Process for generation of acid and for imaging, and imaging medium for use therein |
US5286612A (en) * | 1992-10-23 | 1994-02-15 | Polaroid Corporation | Process for generation of free superacid and for imaging, and imaging medium for use therein |
US5453345A (en) * | 1992-10-23 | 1995-09-26 | Polaroid Corporation | Imaging medium |
US5441850A (en) * | 1994-04-25 | 1995-08-15 | Polaroid Corporation | Imaging medium and process for producing an image |
US5582956A (en) * | 1994-04-25 | 1996-12-10 | Polaroid Corporation | Process for fixing an image, and medium for use therein |
US5631118A (en) * | 1994-04-25 | 1997-05-20 | Polaroid Corporation | Imaging medium |
US5741630A (en) * | 1994-04-25 | 1998-04-21 | Polaroid Corporation | Process for fixing an image, and medium for use therein |
US5488147A (en) * | 1994-07-21 | 1996-01-30 | Minnesota Mining And Manufacturing Company | Diaryliodonium fluoroalkyl sulfonate salts and a method of making |
US5710320A (en) * | 1994-07-21 | 1998-01-20 | Minnesota Mining And Manufacturing Company | Diaryliodonium fluoroalkyl sulfonate salts and a method of making |
US6015907A (en) * | 1996-11-27 | 2000-01-18 | Polaroid Corporation | Trisubstituted pyridine dyes |
US6110638A (en) * | 1996-11-27 | 2000-08-29 | Polaroid Corporation | Process and composition for generation of acid |
US5914213A (en) * | 1996-11-27 | 1999-06-22 | Polaroid Corporation | Process and composition for generation of acid |
US6242154B1 (en) | 1996-11-27 | 2001-06-05 | Polaroid Corporation | Process and composition for generation of acid |
US6307085B1 (en) | 1996-11-27 | 2001-10-23 | Polaroid Corporation | Process and composition for generation of acid |
EP2236488A1 (en) | 2001-03-30 | 2010-10-06 | The Arizona Board of Regents on behalf of the University of Arizona | Materials, methods and uses for photochemical generation of acids and/or radical species |
US20080051553A1 (en) * | 2005-09-20 | 2008-02-28 | General Electric Company | Thermally curable compositions and method |
US8048981B2 (en) | 2005-09-20 | 2011-11-01 | General Electric Company | Thermally curable compositions and method |
US8343608B2 (en) | 2010-08-31 | 2013-01-01 | General Electric Company | Use of appended dyes in optical data storage media |
CN104628540A (en) * | 2013-11-08 | 2015-05-20 | 上海予利化学科技有限公司 | Cation photoinitiator (4-octyloxyphenyl)phenyl iodonium hexafluoroantimonate preparation method |
Also Published As
Publication number | Publication date |
---|---|
DE69012047T2 (en) | 1995-04-06 |
DE69012047D1 (en) | 1994-10-06 |
CA2023392A1 (en) | 1991-05-01 |
FI905354A0 (en) | 1990-10-30 |
ATE110706T1 (en) | 1994-09-15 |
EP0425920A3 (en) | 1991-10-09 |
EP0425920A2 (en) | 1991-05-08 |
JPH03209341A (en) | 1991-09-12 |
EP0425920B1 (en) | 1994-08-31 |
JPH0751524B2 (en) | 1995-06-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4992571A (en) | Method for making octyloxy substituted diphenyl iodonium hexafluoro metalloid salts | |
US6229054B1 (en) | Derivative of cardanol and uses therefor | |
Clark et al. | Position Isomers of Substituted Aryltrimethylsilanes1 | |
JPS6236015B2 (en) | ||
EP0147379B1 (en) | Making nitrodiarylamines | |
JP3508502B2 (en) | Biphenyl derivative having oxetane ring | |
NO890404L (en) | PROCEDURE FOR THE PREPARATION OF PROPARGYLETERS OF HYDROXYAROMATIC COMPOUNDS. | |
US20020193619A1 (en) | Diaryliodonium salt catalysts made from iodotoluene and a method for preparing them | |
EP0545576A1 (en) | Process for the glycidylation of alcohols | |
US4851585A (en) | Vitamin E intermediates | |
JPH07179564A (en) | Production of low viscosity crystalline epoxy resin | |
Son et al. | Selectivity and kinetics of epoxy resin–bisphenol a reaction catalyzed by certain guanidine derivatives | |
US3426046A (en) | Synthesis of epoxides from allylic sulfonium salts | |
US4201878A (en) | Process for producing bisphenols | |
JPS6212772B2 (en) | ||
JPH05222153A (en) | New anthracene-based epoxy resin and its production | |
JPH0655732B2 (en) | Method for producing polyhydric alcohol glycidyl ether | |
JPS642109B2 (en) | ||
US4808736A (en) | Process for the preparation of hydroquinone derivatives and d-α-tocopherol | |
EP0368421B1 (en) | Process for the manufacture of polyglycidylethers | |
US4177211A (en) | Process for the preparation of bis(aminophenyl)alkanes | |
JP2000204136A (en) | Production of liquid epoxy resin | |
JPH0225474A (en) | Production of triglycidyl derivative of aminophenols | |
JPS6111210B2 (en) | ||
JPS5883640A (en) | Preparation of alkylphenol |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: GENERAL ELECTRIC COMPANY, A CORP. OF NY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:FUKUYAMA, JAMES M.;LEE, JULIA L.;CRIVELLO, JAMES V.;REEL/FRAME:005170/0469;SIGNING DATES FROM 19891026 TO 19891027 |
|
FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
FPAY | Fee payment |
Year of fee payment: 4 |
|
FPAY | Fee payment |
Year of fee payment: 8 |
|
FPAY | Fee payment |
Year of fee payment: 12 |
|
AS | Assignment |
Owner name: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT, Free format text: SECURITY AGREEMENT;ASSIGNORS:MOMENTIVE PERFORMANCE MATERIALS HOLDINGS INC.;MOMENTIVE PERFORMANCE MATERIALS GMBH & CO. KG;MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK;REEL/FRAME:019511/0166 Effective date: 20070228 |
|
AS | Assignment |
Owner name: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., A Free format text: SECURITY AGREEMENT;ASSIGNORS:MOMENTIVE PERFORMANCE MATERIALS, INC.;JUNIPER BOND HOLDINGS I LLC;JUNIPER BOND HOLDINGS II LLC;AND OTHERS;REEL/FRAME:022902/0461 Effective date: 20090615 |
|
AS | Assignment |
Owner name: MOMENTIVE PERFORMANCE MATERIALS GMBH & CO KG, GERMANY Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT;REEL/FRAME:054387/0001 Effective date: 20201102 Owner name: MOMENTIVE PERFORMANCE MATERIALS INC., NEW YORK Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT;REEL/FRAME:054387/0001 Effective date: 20201102 Owner name: MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK, JAPAN Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT;REEL/FRAME:054387/0001 Effective date: 20201102 |
|
AS | Assignment |
Owner name: MOMENTIVE PERFORMANCE MATERIALS INC., NEW YORK Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT;REEL/FRAME:054883/0855 Effective date: 20201222 |